It is announced that Prince Hugo will be visiting the castle. Swiftnick plans to rob the coach taking Prince Hugo to the castle, but does not want to use any of Moses' inventions, as he feels they never work. Meanwhile, Sir John wants to please Prince Hugo, as it will make him and the castle look good. Being aware that Prince Hugo is keen on torture, he instructs his inventor to build an ultimate torture machine – only problem is, Sir John drowned his inventor last week! He therefore hires Moses, and gives him a short deadline in which to build his machine, threatening to drown him as well if his invention is not ready on time, or does not work. When Prince Hugo arrives, he complains about having been stopped in the forest by Swiftnick (an attempt which obviously failed). He suggests that a good way to test the new torture machine would be to capture Swiftnick by sundown, and use it on him. At the same time, Swiftnick plans to rescue Moses, feeling that his invention is sure to malfunc

After robbing a coach, Tom realises that he has lost his lucky pants. He decides that it is not safe for him to outlaw anymore, and tells the gang that they should each find a job. Moses sees an advert for a post as a barmaid in the local public house, and decides to go for it. However, when he enters the pub, he discovers that Tom has already got the post. This infuriates Moses, who decides to try a job at the castle. When he arrives at the castle, Captain Watt refuses to give Moses a job. Moses is so desperate that, in a moment of madness, he agrees to reveal Swiftnick's true identity in exchange for a job. Tom is soon arrested and put in the dungeon. He attempts an escape, but fails as he has no confidence without his lucky pants. DeeDee manages to rescue him by disguising herself as Swifnick, to convince Sir John that he has the wrong man. Tom is released, but he does not forgive Moses. Tom refuses to do the next heist with Moses, and so goes alone. However, he has not got his luck

After discovering that Sir John has sold her Father's farmland, Lady Devereux decides to enlist the help of Swiftnick to intercept the delivery of the money gained from the sales. She writes a letter from Lady Devereux to Swiftnick, and then dresses as DeeDee to take the letter to him. After planning the heist in the crypt, Tom, Moses and DeeDee prepare to leave, but then find that the door to the crypt is jammed – there is no other way out. Believing that they will die in the lair, DeeDee decides to write about her experiences, hoping that her Father will find it in later years. There is then a flashback to what happened when they first met. DeeDee speaks of how she was held up by Tom and Moses when she first arrived at the castle. Lady Devereux pulled out a gun, and robbed both boys of their clothing. Later on, Lady Devereux decided to join the outlaw gang, so as to be able to fight against Sir John, stopping him from taking all power from her Father. She dressed as a peasant, DeeDee

Tom, Moses and DeeDee unwittingly take in Sir John's escaped feasting pig, whose milk they bottle and sell in order to raise funds to enter the annual village Box Car Race. When the sow and her piglets are recaptured by Sir John's henchmen, Tom must make a difficult choice between entering the race or saving the bacon.

Village idiot Bardolph blackmails Tom into letting him join and lead the gang after he discovers Tom's outlaw identity. Meanwhile, Sir John's bossy and demanding mother arrives in town, looking for a stupid manservant.

Tom, Moses and Deedee come across a treasure map on April Fool's Day, but realise that they will need Sir John's medallion in order to unlock the treasure. They manage to steal the necklace but leave the map in Sir John's possession, who then joins in the search for the treasure himself. How will the outlaws outfox their enemy, and is the treasure all it seems?

Deedee meets her match in Felix, the charming and handsome son of a wealthy widow, who takes a liking to her. When Moses decides to kidnap the young chap, Deedee rejects the plan, but the gang must come to Felix's rescue when Sir John's guards abduct him.